I've noticed that there seems to be a little bit of debate around here about how having certain paths not make certain turns or having towns in slightly incorrect proportions or incorrect positions is qualified as not being "lore-friendly".
I would like to assure everyone that there is no "correct" placement for certain landmarks. You see, the exact scale of Tamriel is actually a commonly debated topic among loremasters, and I can assure you that all discussions have concluded that the depiction of provinces within the game is frankly incorrect.
The best and most recent source we have for an accurate scale of Nirn comes straight from Michael Kirkbride, and looks like this:

Yup. According to this map, Vvardenfell is more than four times larger than the entirety of Spain and Portugal. The sheer size of Red Mountain alone is enough to boggle the mind. So I recommend that every dedicated developer here try not be intimidated by making changes- because no matter what, you'll be wrong, which is a good thing. :)

Skyrim's engine bugs up after 64-64 cells. This makes it impossible to make things that are like 100 square miles let alone tamriel's estimated 12 million. The games themselves are only lore friendly, not lore themselves.(other wise you can't reconcile the books. The games and the books cant both be right) the scale from game to game is even off. the only reason people debate what to do is because we what to make it a close to a real life tamriel as possible